The Roommate Agreement
by storiestobetold
Summary: AU/AH: Elena is in need of a new roommate and her only option is Damon Salvatore.
1. Chapter 1

**The Roommate Agreement**

* * *

Shit. It was already seven in the afternoon and here she was pacing through the streets of New York City with a box full of streamers and god knows what else. The inside of the box looked like a unicorn exploded and got glitter on every damn thing. Of course, Caroline would pick the most extravagant decorations for this special occasion. It was Caroline's birthday, and according to Caroline, she might as well throw her own damn party herself instead of getting a surprise one where her tasteless friends end up doing everything wrong. Shit. Now it was 7:15 and she might as well stab herself before Caroline got the knife prepared. It wasn't her fault anyways. She was busy checking out new apartments since she got kicked out of her old one. Let's just say her last break up didn't end well. She reached the cross walk and the yellow box indicated that she had five seconds left to cross the street. With all her speed, she rushed across the street and pushed through the doors of The Grill.

"I got here in one piece Care; please don't break me in two."

"Just give me the box and go blow up some balloons. Everyone will be here in thirty minutes so that gives us enough time to rush and maybe, just maybe, make this shitty place look halfway decent."

"I'm on it! Plus who cares what this place looks like? When we get wasted tonight, it'll look like the freaking Taj Mahal!"

"Just hurry up Gilbert, I need some alcohol in my system to blur out all this tacky décor. Meet me in the back in ten, we gotta make ourselves pretty for tonight!" Caroline yelled as she left the room.

Elena slumped in her chair as she blew yet another balloon. This was the first time she was single in years. She'd been with Matt since high school and stayed with him because it felt comfortable. He'd been the guy you could imagine yourself having a family with, white picket fence and all its glory. In her mind, there were always doubts and it wasn't until last week that she'd voiced it out loud. She called their relationship 'boring and uninteresting' and he took to heart. She'd never seen him so hurt; he told her she needed to leave. And she did. Now all she needed to do was find somewhere else to live. She'd figure out tomorrow, because for tonight she'd forget that she was basically homeless and have a kick ass time with her best friend.

* * *

Elena looked in the mirror for the hundredth time that night. Her strapless black lace dress fit her curves perfectly while her brunette locks framed her face in loose curls. Black pumps and red lips. She added silver earrings and turned around to face Caroline. Oh, Caroline. She was always a vision. She wore a bright red one shoulder dress and black studded high heels. Her perfect blonde curls bounced lightly and her bright blue eyes shined through her sparkly gold eye shadow. Caroline's mouth dropped open as she stared at Elena.

"Elena Gilbert. You look hot as fuck." Caroline whistled.

"Thanks, Care. You look pretty fuckable yourself." Elena giggled.

"Are you ready to have a fun night? No stress. You know I hate it when you stress."

"Well, lucky for you. Tonight will be stress free. No brooding on my part."

"Excellent. Because, tonight, and for one night only. I'll be your professional wing woman."

"You'll be the Barney to my Ted?"

"Gladly. Now let's go. Everyone is waiting to be graced with our presence."

* * *

A swarm of bodies crowded Elena and Caroline as soon as they entered. They all screamed "Happy Birthday!" in half drunken slurs. It seemed that everyone got buzzed while they got dressed, what a surprise. She hugged every member of their group before heading over to the bar to get some well needed space. She wasn't going to ruin Caroline's night, but she needed a drink to cheer herself up before she could become the life of the party. Stefan caught her brooding for just about five seconds and walked over to give her the Salvatore pep talk.

"Chin up, kid. This is a party, not a funeral." Stefan said with a sense of authority.

"Thanks for the fatherly advice, Stef."

"Come on, Lena. Matt's one of my best buds but we all knew from the start that you two wouldn't last."

"And why is that? It's because I suck, right? Totally, completely suck. I'm the worst. Oh god, I _am_ the worst. How could I hurt Matt? Of all people! Poor, innocent Matt." Elena exclaimed and rested her head on the counter. Hitting her head a couple of times before giving up and hanging her head in shame.

"Elena, it's not your fault. You and Matt didn't work because you don't want the same things in life. Your paths just don't line up with each other and you can't blame yourself for that."

"That's the thing, Stefan. I don't know what I want in life. All I know is that I'm too scared to even try.

Stefan lifted her chin up to meet his eyes. He gave her meaningful look and tug his lips into a comforting smile.

"Elena, I've known you for years. You're destined for something great, kid. I know that Caroline and I are like the parents of this insane group of friends we have and we'd be lying if we said you weren't our favorite. We're rooting for you, all you have to do meet us halfway. It's New York, endless possibilities right at your feet. So, let's get you a drink, preferably something strong, and have fun tonight, for Caroline's sake."

Elena smiled warmly and hugged Stefan with all her strength. He always knew what to say and the right times to say it. Now she'd just need to follow his advice. She turned to get the attention from the man behind the bar.

"Hello Mr. Bartender, I would like thirty shots of tequila please."

* * *

"One. Two. Three!"

The group of friends all tilted their heads back to consume the fifth round of tequila they had drunk that night. They all looked at each other and laughed, eyesight hazy and dizzy thoughts rushing through their system.

"We should buy a bar!" Bonnie shouted as if it was the greatest idea ever known, her eyes wide with excitement. The group gasped with pleasure.

"Wait guys…we should buy this bar!" Caroline screamed as the group gasped even louder.

A man with tousled brown hair walked over, smile intact at the customers in front of him. He leaned over by their booth and whispered.

"You guys know that I own this bar, right?"

"Ric!" They all screamed way too loudly, as if all their hearing had been impaired.

"Scream any louder and I think you might send a signal to outer space." Ric replied and walked over to the other customers.

"Woah. Outer Space." Tyler said to himself, clearly stuck in his thoughts.

"Do you think aliens are real? Like what if they come to kill us one day?" Jeremy asked with his eyes shot open as if he'd seen a ghost.

"Dude. Aliens are totally real. The CIA are keeping them locked away somewhere. Everyone knows that." Stefan stated with complete confidence.

"Guys, aliens are more afraid of us and we are afraid of them. Poor little aliens, so misunderstood." Caroline pouted and sulked into the cushiony surface of the booth.

They all went into a temporary silence of thought. Mouths wide open and staring at the ceiling.

"I miss Matt." Elena whimpered, saying her thoughts out loud.

Everyone faced towards her, sympathetic smiles on each of their faces, completely sobered up by her words.

"I invited him, but he said he'd rather 'sit this one out'. Just give it time, 'Lena." Caroline confessed, her hand on Elena's arm in a comforting gesture.

"You guys are friends with him too. It isn't fair of me to make you guys choose between us. I ruined the group. I'm sorry guys, I ruin everything. I even ruined tonight." Elena mumbled, eyes watery with tears.

"Elena, come on. I can't say that this doesn't change things but you haven't ruined anything. We're still going to hang out with Matt and we're still going to hang out with you. It'll take time but eventually those two will merge together and we'll go back to being the seven co-dependent freaks who get drunk every week and tell each other our sob stories." Bonnie pleaded, wisdom intact.

The group shared a small laugh and the mood instantly brightened.

"Besides, Matt might be one of my best friends, but at least I don't have to hear about my sister's sex life all the time." Jeremy joked.

"And we don't have to see you two getting heavy on the PDA either." Tyler added.

"Thanks guys, tell me how to really feel." Elena replied sarcastically.

The loud ring of a cell phone interrupted the moment and everyone faced towards Stefan. He took his phone out of his pocket and looked at the screen of his phone. He stilled, shock shown all over his face. He slid out of the booth and took the call outside of the bar. The group stared at him quizzically as he walked away.

"Who do you think it is?" questioned Jeremy.

"I don't know, I've never seen him like that before." Caroline said, concerned.

"Well whoever it is, is clearly bad news." Bonnie stated.

"Stefan never really talks about his family; you think it's his dad?" Tyler suggested.

"Maybe, I guess we'll find out." Elena said quickly as Stefan entered back into the bar.

He looked unhappy and hopeful at the same time. His body was tense as he slipped into the booth. All eyes were on him, so he sighed and shook his head.

"My brother called."

* * *

**A/N: Cliffhanger! This chapter focuses mainly on the group but we'll get to meet Damon in the next chapter. Feedback is always appreciated!**


	2. Chapter 2

**A/N: **I'm back! With a bucket load of inspiration! Hope you enjoy.

"Hey little bro. Long time, no see."

Damon walked into the Grill full of confidence, same as always, thinking the world should drop down and worship at his feet. His good looks and witty charm paved a way for him to always get what he wanted but the problem was that Damon Salvatore didn't really know what he needed. All the parties, the women, the alcohol drove his little brother away and he was left to figure out life all on his own. He pushed his brother away, practically shoved him out the door himself, suitcase packed and all. Ever since their mother died, his life went downhill and he never learned how to climb back up. Hopefully, his saint of a brother could forget his shitty past and give him a place to crash for a while. California was fun while it lasted but he needed a clean slate, and what was cleaner than New York City. Well, almost everything, but not the point.

"And the prodigal son returns!" Stefan delivered sarcastically. There could only be two reasons for his brother's return. Money or ….money. Wait. Make that one reason. Sadly, he was tight on money himself.

"Don't be an ass, Stefan. Can't a big bro come see his little bro for some quality bro time? You up for a game of football? You always loved when I'd let you win." Damon grinned, tugging on the sentimental strings his brother had for family.

"I'm sorry, Damon. Can't hear you through the bullshit you're pulling." Stefan wasn't falling for nice brotherly act he'd gone through before. Love 'em and leave 'em, the Damon Salvatore motto.

"Oh, Stefan. Never underestimate my love for you. In fact, I love you so much that I've decided to stay in New York. Permanently. No leaving this time, I promise." Damon patted on his heart and walked over to his little brother. "Pinky swear?"

Stefan chuckled, he knew better than to trust his brother. "Where you gonna stay, huh?"

"Hopefully with my loving brother? We can be roomies again…just minus the bunk beds. "

"No can do. Caroline, my girlfriend, kind of occupies my place right now. I'm afraid you're gonna have to man up and find a place of your own, big bro." Stefan patted his brother on the back and walked out the door. He wasn't going to help a lost cause and his brother was the most lost cause on the planet.

* * *

"Two bedrooms, one bathroom. Looking for someone over 21."

"That sounds pretty good!" Caroling squeaked while painting her toenails a bright shade of blue.

"…Must be cool with college parties every weekend and loud music."

"And good turns into bad. Elena, don't worry. You can stay on my couch as long as you need to!"

"Thanks, Caroline. But I'm being such a third wheel with you and Stefan. I need to find a place soon or I'm gonna live out on the street. Do you have cardboard? I should make a sign. How does 'Will give hugs for a home' sound?"

"Elena! Don't joke around like that. You are not going to be homeless." Caroline grasped her hands on her friend's shoulder. "You are Elena Gilbert. This is New York City. There is somewhere out there for you and you will find it."

"You and Stefan can go around giving me pep talks but the world hates me and I'm going to end up sleeping on the subway." Elena sighed. Breaking up with Matt had left her in a sucky mood and all this inspiring crap was well …crap.

The apartment door opened and Stefan walked in mumbling a whole bunch of nonsense. He walked to the fridge, grabbed and beer and plopped down on the couch next to them.

"Stupid brothers, they're like leeches. Sucking onto everything you have. I swear, if he thinks he can just walk into my life and act like that then he can go shove his brotherly love right up his self-righteous ass."

Caroline and Elena stared shockingly at him. Stefan Salvatore, never the one to talk bad about anyone was trash talking his own brother of all people. Someone should've pinched them because Saint Stefan had gone and been replaced with Satan Stefan.

"What? If I'm gonna talk shit about someone it might as well be about my darling big brother." Stefan said, taking a sip of his beer and grabbing the remote.

"Babe? You okay?" Caroline quietly said with worry. Stefan never got this worked up over anything.

Stefan sighed. "My big bro is back in town and wants to live with me. I mean, he can't just waltz into our place and sleep on our couch forever. Who even does that?"

Elena got up and awkwardly walked to the kitchen.

"Oh shit. Sorry 'Lena. I wasn't talking about you. You know you can stay however long you want to. It's just that he's got me all tense and I didn't mean to take it out on you."

"It's okay Stefan, I'm gonna go. Search for apartments and stuff. Meet me at the grill later for dinner?"

"Sure, be there at eight!" Caroline squeaked.

* * *

Elena dragged herself into the Grill and slumped onto a seat at the bar. Everywhere she went looking had some huge flaw, she just wanted a nice place to live not a trashy apartment with college dudes checking her out every minute. Waving a finger to signal Alaric, he arrived instantly.

"Elena Gilbert with a frown? That's not a good sign."

"Speaking of signs, do you have any cardboard? I might need it with the way things have been going."

"No cardboard, but I do have alcohol and that's always the better alternative." Alaric grinned and poured her favorite bourbon into a glass.

"Hello bourbon, you are going to be my best friend for a while. Never leave me, okay?" Elena gulped it all down and signaled for another. A voice from across the bar caught her attention.

"Hot girl who drinks bourbon, I think I might be in love."

Elena groaned. Some douche hitting on her at a moment of weakness. So fucking cliché.

"I think I might punch you in the face but you don't see me shouting it out like some pretentious asshole."

"Ouch. And she's feisty. What's got your panties in a twist? Wait. Don't answer that. Hopefully, the answer is me."

Elena turned around to see this guy who had the nerve to act like she'd jump into his bed as soon as he called. God, men these days. They think they can make some sexist comment, add some alcohol and get themselves laid. Well, hell fucking no. She was going to give this asshole a piece of her mind. She turned around, witty comment prepared and all.

"Actually, the answer is go fuck yourself."

Holy shit. This asshole was actually pretty fucking hot.

"Well. What does a guy say to a response like that?"

"He buys me another drink to make up for his flirty little comments and then leaves the hot girl to drink her bourbon in peace."

"Hey bartender. Two bourbons, one for me and one for the lady."

Alaric poured the drinks and made eye contact with Elena. He was always protecting her from the drunken guys at the bar. She gave him a look to just leave it alone. She could handle this guy, he wasn't dangerous, he was just entirely full of himself.

Damon slid her drink down the bar. "A peace offering, milady."

"Thanks." She gulped it down without any hesitation. Damon stared in awe. This girl was like a female version of him. And what's better than fucking yourself, right?

Alaric felt the weird silence between them so he intervened.

"So, 'Lena, find a new place to live yet?"

"Ugh, everyone in the entire New York City is either a pervert or an asshole. Mostly both. Consider me homeless."

Damon chuckled. He had just charmed his way into getting a pretty decent apartment. The sales lady fell for his famous smirk and offered it at half the price. Just the perks of being Damon Salvatore. Now here he was sitting next to a hot girl who needed somewhere to stay. Perfect fucking timing.

"Permission to speak, milady?"

"Buy me drinks for the whole night and you can say whatever the fuck you want."

"Deal."

Damon slid over the bar stool next to her put his hand out for her to shake it. Obviously, Elena ignored his gesture.

"It just happens that I just recently bought a two bedroom apartment, and wouldn't it be awfully kind of me to help a fellow bourbon drinker out?"

Elena was actually just drunk enough to consider his offer. Just for a while, not permanently. Maybe she could con this jerk into letting her stay for free, with certain conditions of course. Let this jerk believe she was interested in him and have somewhere to crash until she found some place more stable. Sounded like a great fucking plan. Elena was actually proud of herself for thinking this through.

"And what would be in it for you?"

"Some good company is all I'm looking for."

"And that's all you'd want from me."

"Well, some rent would be nice."

"But, I'm not nice."

"Well, if I'm not making a profit from this, I really don't see the point here."

Elena leaned in closer and put her hand on his leg. Flirting with dumb guys was always easy. All they needed was a simple touch and they were wrapped around her fingers. Moving her mouth to his ear, she leaned in even closer.

"The point is. I can be nice sometimes. And if you're lucky, you'll see just how nice I can be." She breathed. Smiling at him, he was so entirely whipped it was actually adorable. "Do we have an agreement?"

"Oh, we have the greatest agreement in the world, sweetie." Damon smirked. All it took was a little charm and this girl was already moving in with him and offering him free sex. How could he refuse?

Elena laughed flirtatiously and grabbed his hand. "Now take me home so we can make it official, huh?"

Damon leaded her out of the Grill quickly but bumped into some douche in his way.

"Hey buddy, are you fucking blind?" Damon looked up to see who this guy thought he was. Oh shit.

"Damon?"

"Stefan?"

"Elena?"

"Stefan?"

"Little bro, you know my girl? It's a small world."

**A/N:** Sooooo, what do you think? Is there too much cursing? I mean, that's how people talk anyways. At least in New York they do. Anyways please leave comments and constructive criticism. Be mean if you have to, it'll only make me a better writer. Also, if anyone is interesting in being a beta for this story that would be awesome! PM if you want to be considered.


	3. Chapter 3

**A/N:** Wow I don't even know where all of this came from. I love the Caroline and Elena dynamic and I wanted to state the whole premise of the story too, so here you go! Hope you like it! *fingers crossed*

"So…you're dating Stefan's brother?" Caroline questioned. She couldn't quite wrap her head around this whole complicated weird ball of a situation.

"I wouldn't say dating." Elena replied. How the hell was she supposed explain her stupid drunken plan to her best friend?

"Then, what are you doing? I mean, leaving a bar together and holding hands pretty much mean you guys were totally going to f-

"Caroline!"

"What? Just stating the obvious. I mean, you're acting like you hate him yet you leave with him in hand holding matrimony. If you aren't doing the deed then what the hell are you doing, Elena?"

Elena sighed deeply. Her friend was either going to think she was a total psycho or a complete genius. She wasn't even sure which one she was herself.

"He offered me a place to stay. And I kind of said yes?" Elena shrugged. Not sure how to get the whole point across.

Caroline scoffed. "So. You're telling me. A guy. Scratch that. A hot piece of man sits next to you at a bar and offers you a home. And this guy is a complete stranger, yet you say yes. And you leave together with some kind of freaky sexual energy? Did I get that right? Please tell me I didn't because this makes no sense at all. Ugh, I need a drink. Alaric!"

"What do you need, sweetheart? Looks like your brains about to burst." Alaric counted the wrinkles on her forehead. Tequila would fix that up in a second.

"How about the strongest alcohol you have for me and some common sense for Elena?"

"Caroline!"

"Elena! Explain yourself or I'm going to drink myself to death trying to figure out why you would live with a stranger over your best friend! I mean, are you mentally ill? I'm actually seriously worried for you!"

"Stop ranting. Just calm down, Care. Have a drink for gods sake. You're acting like my mother." Elena sighed. The girls took a couple of shots and got trapped in their thoughts for a while.

"'Lena, come on."

"Care, you're gonna think I'm the worst person ever."

"Nothing in the world can ever make me think less of you, Elena. We went to college together, I know all your dirty secrets. Like that time when you sucked-

"Caroline!"

"Sorry!"

"Okay fine. I was going to lead him on for a free place to crash. I know I'm a total bitch for even thinking about that but he was being an asshole and totally had it coming and I had too much to drink and I just-

"Elena!"

"What?"

"You're ranting."

"Sorry."

Caroline put her hand one Elena's shoulder and her sympathetic look was on full power.

"Damon's a dick. I know. Stefan has told me all about his lovely asshole of a brother. Whatever you were thinking about doing, he probably deserved it. You're not a bitch. You're a smart girl who took advantage of a dumb boy and to be honest, I'm kinda impressed." Caroline giggled.

"Really?"

"Yeah, I thought I was good at scheming but you're clearly the winning champion."

The girls laughed and all the stress from the conversation before was completely gone.

"You know, I'd go for it."

"What?"

"Your plan. I mean, it's about time someone fucked Damon Salvatore over instead of the other way around."

"You're serious?"

"Totally! Love 'em and leave 'em. The Damon Salvatore motto. Stefan told me all about it. He probably would have taken advantage of you anyways. You two are a match made in heaven. He wants sex, you want a home. You could make it work."

"There's one problem…I don't wanna have sex with him."

"Ummm, Elena. Are you blind? Do you need glasses? I'm worrying about your mental state again."

Elena laughed. "Care, he's a total jerk. Even if he's gorgeous, I don't sleep around. Never have, never will. I'm an old fashioned relationship kind of girl."

"Then what were you planning to do? Fake having sex with him? How would that even work?"

"I don't know. I guess, I'd just lead him on. Tell him I don't have sex on the first date. That it takes me a while to be comfortable with a guy to be in that position."

"And you think sex-god Damon Salvatore would actually wait for you to 'be comfortable'?"

"Well, guys love the chase. And Damon looked at me and I saw it. That look. He'll probably do anything to sleep with me. It's all a game to him. Might as well play too."

"Ooo. This sounds so sneaky! Like John Tucker Must Die! Oh my god! We should rent that movie and write down some of their ideas! It'd be totally fun! I call being Sophia Bush! She's totally hot!"

"Care!" Elena tried to hold in her laughter. Sometimes Caroline could get so excited it looked like she'd go into a mild seizure. I mean, the girl was surely passionate about scheming.

"Can you do it? Please Elena? I need some excitement in my life and living vicariously through you has always been fun! "

"I don't know. If I actually go through with it, you can't tell Stefan. I don't think he'd approve. As much as he hates his brother, he loves him too."

"My lips are sealed Elena Gilbert. It's time for the player to get played."

**A/N:** I wasn't planning to go in this direction when I started this story but I guess my mind decided to go on another route. What do you think? I LOVE writing dialogue because I suck at describing inner thoughts and all that mumbo jumbo (did I really just say that). Anyways, I need feedback! More feedback means quicker updates because I'm totally out of my writers block right now and full of inspiration!


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